DE602004012736T2 - Trennung von glyoxaldiacetalen durch flüssig-flüssig-gegenstromextraktion - Google Patents
Trennung von glyoxaldiacetalen durch flüssig-flüssig-gegenstromextraktion Download PDFInfo
- Publication number
- DE602004012736T2 DE602004012736T2 DE602004012736T DE602004012736T DE602004012736T2 DE 602004012736 T2 DE602004012736 T2 DE 602004012736T2 DE 602004012736 T DE602004012736 T DE 602004012736T DE 602004012736 T DE602004012736 T DE 602004012736T DE 602004012736 T2 DE602004012736 T2 DE 602004012736T2
- Authority
- DE
- Germany
- Prior art keywords
- glyoxal
- diacetal
- solvent
- mixture
- liquid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 title claims abstract description 182
- 229940015043 glyoxal Drugs 0.000 title claims abstract description 91
- 238000000622 liquid--liquid extraction Methods 0.000 title claims abstract description 14
- 238000000638 solvent extraction Methods 0.000 title claims abstract description 14
- 238000000926 separation method Methods 0.000 title claims description 13
- 239000000203 mixture Substances 0.000 claims abstract description 42
- 238000000034 method Methods 0.000 claims abstract description 39
- 239000002904 solvent Substances 0.000 claims abstract description 30
- 238000000605 extraction Methods 0.000 claims abstract description 18
- 239000011541 reaction mixture Substances 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 60
- ZETHHMPKDUSZQQ-UHFFFAOYSA-N Betulafolienepentol Natural products C1C=C(C)CCC(C(C)CCC=C(C)C)C2C(OC)OC(OC)C2=C1 ZETHHMPKDUSZQQ-UHFFFAOYSA-N 0.000 claims description 34
- PCSMJKASWLYICJ-UHFFFAOYSA-N Succinic aldehyde Chemical compound O=CCCC=O PCSMJKASWLYICJ-UHFFFAOYSA-N 0.000 claims description 34
- HEOKFDGOFROELJ-UHFFFAOYSA-N diacetal Natural products COc1ccc(C=C/c2cc(O)cc(OC3OC(COC(=O)c4cc(O)c(O)c(O)c4)C(O)C(O)C3O)c2)cc1O HEOKFDGOFROELJ-UHFFFAOYSA-N 0.000 claims description 34
- OGFKTAMJLKHRAZ-UHFFFAOYSA-N 2,2-dimethoxyacetaldehyde Chemical compound COC(OC)C=O OGFKTAMJLKHRAZ-UHFFFAOYSA-N 0.000 claims description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 33
- 238000006359 acetalization reaction Methods 0.000 claims description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 16
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 11
- 238000004821 distillation Methods 0.000 claims description 11
- 239000012429 reaction media Substances 0.000 claims description 7
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
- 150000002170 ethers Chemical class 0.000 claims description 3
- 239000012535 impurity Substances 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 239000003377 acid catalyst Substances 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims 1
- 239000007788 liquid Substances 0.000 abstract description 8
- 239000012071 phase Substances 0.000 description 24
- 239000000243 solution Substances 0.000 description 7
- 229920001429 chelating resin Polymers 0.000 description 6
- 238000009826 distribution Methods 0.000 description 6
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000003729 cation exchange resin Substances 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- 239000002638 heterogeneous catalyst Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 238000005192 partition Methods 0.000 description 2
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- VPZFYLQMPOIPKH-UHFFFAOYSA-N 1,1,1,2-tetramethoxyethane Chemical compound COCC(OC)(OC)OC VPZFYLQMPOIPKH-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- -1 cyclic acetals Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 235000020030 perry Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- HVZJRWJGKQPSFL-UHFFFAOYSA-N tert-Amyl methyl ether Chemical compound CCC(C)(C)OC HVZJRWJGKQPSFL-UHFFFAOYSA-N 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- ZXAUZSQITFJWPS-UHFFFAOYSA-J zirconium(4+);disulfate Chemical compound [Zr+4].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O ZXAUZSQITFJWPS-UHFFFAOYSA-J 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/48—Preparation of compounds having groups
- C07C41/58—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/30—Compounds having groups
- C07C43/303—Compounds having groups having acetal carbon atoms bound to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/80—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/02—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen
- C07C47/198—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen containing ether groups, groups, groups, or groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0306168 | 2003-05-22 | ||
| FR0306168A FR2855171B1 (fr) | 2003-05-22 | 2003-05-22 | Procede de separation d'un diacetal du glyoxal d'un melange brut le contenant par extraction liquide-liquide a contre-courant |
| PCT/FR2004/001224 WO2004106274A1 (fr) | 2003-05-22 | 2004-05-18 | Separation d’un diacetal du glyoxal par extraction liquide-liquide a contre -courant |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE602004012736D1 DE602004012736D1 (de) | 2008-05-08 |
| DE602004012736T2 true DE602004012736T2 (de) | 2009-04-16 |
Family
ID=33396672
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE602004012736T Expired - Lifetime DE602004012736T2 (de) | 2003-05-22 | 2004-05-18 | Trennung von glyoxaldiacetalen durch flüssig-flüssig-gegenstromextraktion |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US20070073088A1 (zh) |
| EP (1) | EP1625108B1 (zh) |
| JP (1) | JP4643580B2 (zh) |
| KR (1) | KR100924181B1 (zh) |
| CN (1) | CN100349843C (zh) |
| AT (1) | ATE390398T1 (zh) |
| DE (1) | DE602004012736T2 (zh) |
| ES (1) | ES2302009T3 (zh) |
| FR (1) | FR2855171B1 (zh) |
| TW (1) | TWI300408B (zh) |
| WO (1) | WO2004106274A1 (zh) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102005011720A1 (de) * | 2005-03-15 | 2006-09-21 | Clariant Produkte (Deutschland) Gmbh | Neue amphiphile Acetale |
| DE102005011719A1 (de) * | 2005-03-15 | 2006-09-28 | Clariant Produkte (Deutschland) Gmbh | Wasch- und Reinigungsmittel enthaltend Acetale als organische Lösemittel |
| DE102005011722B4 (de) * | 2005-03-15 | 2010-04-08 | Clariant Produkte (Deutschland) Gmbh | Verfahren zur chemischen Reinigung von Textilmaterial |
| US9308879B2 (en) * | 2008-08-06 | 2016-04-12 | Honeywell International Inc. | Method, system, and apparatus of vehicle and fleet operator profile automation and deployment |
| US8224348B2 (en) * | 2009-12-18 | 2012-07-17 | Trueposition, Inc. | Location intelligence management system |
| US9386421B2 (en) | 2009-12-18 | 2016-07-05 | Trueposition, Inc. | Location intelligence management system for border security |
| FR2955322B1 (fr) * | 2010-01-21 | 2013-09-06 | Rhodia Operations | Procede de fabrication d'un hydroperoxyde d'alkyle |
| CN102895998B (zh) * | 2012-09-19 | 2015-07-15 | 湖北省宏源药业科技股份有限公司 | 一种强酸型固体催化剂及其制备方法和应用 |
| CN103242145A (zh) * | 2013-04-27 | 2013-08-14 | 南京工业大学 | 乙二醛制备乙二醛单缩醛和二缩醛的方法 |
| CN105481667B (zh) * | 2016-01-12 | 2017-12-22 | 西安近代化学研究所 | 一种提纯2,2‑二甲氧基乙醛的方法 |
| CN112451993B (zh) * | 2020-11-25 | 2022-02-01 | 中国石油化工股份有限公司 | 一种喷淋萃取设备和溶剂萃取方法 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2194405A (en) * | 1940-03-19 | Process of producing tetba-acetals | ||
| GB559362A (zh) * | 1900-01-01 | |||
| US3130234A (en) * | 1964-04-21 | Process for producing glyoxal | ||
| US2360959A (en) * | 1944-10-24 | Process of making tetra-acetals | ||
| US559362A (en) * | 1896-05-05 | Spalt-dropper for rotary shingle-sawing machines | ||
| DE311142C (zh) * | 1915-06-04 | 1919-02-27 | ||
| US2081719A (en) * | 1932-05-11 | 1937-05-25 | Shell Dev | Solvent extraction process |
| US2321094A (en) * | 1941-03-18 | 1943-06-08 | Carbide & Carbon Chem Corp | Tetraacetals of glyoxal with glycol monoethers and process of making them |
| US3860656A (en) * | 1972-06-08 | 1975-01-14 | Union Carbide Corp | Purification of glyoxal |
| DE2428081C3 (de) * | 1974-06-11 | 1981-02-19 | Chemische Werke Huels Ag, 4370 Marl | Kontinuierliches Verfahren zum Reinigen von Glyoxal |
| JPS5636425A (en) * | 1979-09-03 | 1981-04-09 | Daicel Chem Ind Ltd | Preparation of acetaldehyde dimethyl acetal |
| US4835320A (en) * | 1986-06-03 | 1989-05-30 | Societe Francaise Hoechst | Process for the preparation of glyoxal monoactals |
| JP2754216B2 (ja) * | 1988-07-29 | 1998-05-20 | ダイセル化学工業株式会社 | アセトアルデヒドジメチルアセタールの製造法 |
| US5191127A (en) * | 1991-08-13 | 1993-03-02 | Loyola University Of Chicago | Glyoxal derivatives and method for making the same |
| FR2700535B1 (fr) * | 1993-01-19 | 1995-04-14 | Hoechst France | Procédé continu de fabrication industrielle du diméthoxyéthanal. |
| CN1039409C (zh) * | 1994-04-01 | 1998-08-05 | 清华大学 | 溶剂萃取法纯化乙二醛水溶液方法 |
| DE19651325A1 (de) * | 1996-12-11 | 1998-06-18 | Basf Ag | Verfahren zur Herstellung von Glyoxalmonoacetalen |
| NL1013971C1 (nl) * | 1999-12-28 | 2000-03-22 | Antonius Johannes Cornelis Van | Werkwijze ter vervaardiging van gefigureerde elementen. |
| DE10149063A1 (de) * | 2001-10-05 | 2003-04-17 | Basf Ag | Verfahren zur Herstellung von Diacetalen des Glyoxals |
-
2003
- 2003-05-22 FR FR0306168A patent/FR2855171B1/fr not_active Expired - Fee Related
-
2004
- 2004-05-17 TW TW093113830A patent/TWI300408B/zh not_active IP Right Cessation
- 2004-05-18 AT AT04742769T patent/ATE390398T1/de active
- 2004-05-18 US US10/557,920 patent/US20070073088A1/en not_active Abandoned
- 2004-05-18 DE DE602004012736T patent/DE602004012736T2/de not_active Expired - Lifetime
- 2004-05-18 ES ES04742769T patent/ES2302009T3/es not_active Expired - Lifetime
- 2004-05-18 WO PCT/FR2004/001224 patent/WO2004106274A1/fr active IP Right Grant
- 2004-05-18 KR KR1020057022184A patent/KR100924181B1/ko not_active IP Right Cessation
- 2004-05-18 JP JP2006530363A patent/JP4643580B2/ja not_active Expired - Fee Related
- 2004-05-18 EP EP04742769A patent/EP1625108B1/fr not_active Expired - Lifetime
- 2004-05-18 CN CNB2004800140340A patent/CN100349843C/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP4643580B2 (ja) | 2011-03-02 |
| EP1625108A1 (fr) | 2006-02-15 |
| TWI300408B (en) | 2008-09-01 |
| WO2004106274A1 (fr) | 2004-12-09 |
| CN1795157A (zh) | 2006-06-28 |
| KR20060021319A (ko) | 2006-03-07 |
| DE602004012736D1 (de) | 2008-05-08 |
| JP2007502318A (ja) | 2007-02-08 |
| FR2855171B1 (fr) | 2005-08-05 |
| US20070073088A1 (en) | 2007-03-29 |
| ES2302009T3 (es) | 2008-07-01 |
| CN100349843C (zh) | 2007-11-21 |
| EP1625108B1 (fr) | 2008-03-26 |
| TW200500331A (en) | 2005-01-01 |
| ATE390398T1 (de) | 2008-04-15 |
| FR2855171A1 (fr) | 2004-11-26 |
| KR100924181B1 (ko) | 2009-10-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8328 | Change in the person/name/address of the agent |
Representative=s name: MEISSNER, BOLTE & PARTNER GBR, 80538 MUENCHEN |
|
| 8364 | No opposition during term of opposition |